3-[2-(methylamino)ethyl]-1H-indol-5-ol

• ChemBase ID: 128517
• Molecular Formular: C11H14N2O
• Molecular Mass: 190.24166
• Monoisotopic Mass: 190.11061308
• SMILES: Oc1cc2c(cc1)[nH]cc2CCNC
• Canonical SMILES: CNCCc1c[nH]c2c1cc(O)cc2
• InChI: InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3
• InChIKey: ASUSBMNYRHGZIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(methylamino)ethyl]-1H-indol-5-ol
• IUPAC Traditional name: N-methylserotonin
• Synonyms: 3-[2-(Methylamino)ethyl]-1H-indol-5-ol; 3-[2-(Methylamino)ethyl]indol-5-ol; 5-Hydroxy-N-methyltryptamine; 5-Hydroxy-Nω-methyltryptamine; N-Methyl-5-hydroxytryptamine; N-Methylserotonin; N-Methyl Serotonin; Norbufotenin; N_ω-Methylserotonin; N-Methyl-5-hydroxytryptamine; N-Methylserotonin

Database IDs

• CAS Number: 1134-01-6
• PubChem SID: 162222824
• PubChem CID: 150885
• Chemspider ID: 132989
• Wikipedia Title: N-Methylserotonin

CALCULATED PROPERTIES

• Acid pKa: 9.450406
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -1.610599
• LogD (pH = 7.4): -1.0300375
• Log P: 0.6882991
• Molar Refractivity: 57.1284 cm^3
• Polarizability: 23.149506 Å^3
• Polar Surface Area: 48.05 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M326595

N-Methylserotonin is the N-methylated derivative of serotonin with similar activity. Studies have identified N-Methylserotonin as a potential active constituent that contributes to the serotonergic activity of black cohosh.

REFERENCES

• Powell, S.L. et al.: J. Agric. Food Chem., 56, 11718 (2008)
• Mais, D.E. et al.: J. Chrm. Biomed. Appl., 225, 27 (2008)